organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain ...

, phosphinites are

organophosphorus Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarb ...

compounds with the formula . They are used as ligands in

homogeneous catalysis In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst in a solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in d ...

and

coordination chemistry A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

Preparation

Phosphinites are prepared by

alcoholysis In chemistry, solvolysis is a type of nucleophilic substitution (S1/S2) or elimination where the nucleophile is a solvent molecule. Characteristic of S1 reactions, solvolysis of a chiral reactant affords the racemate. Sometimes however, the ster ...

of organophosphinous chlorides. For example, treatment of

chlorodiphenylphosphine Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is ...

with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...

and base gives methyl diphenylphosphinite: :ClPPh₂ + CH₃OH → CH₃OPPh₂ + HCl Although they are

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s of phosphinous acids (R₂POH), phosphinites are not made via such intermediates.

Reactions

Oxidation of phosphinites gives phosphinates: :2 P(OR)R₂ + O₂ → 2 OP(OR)R₂ Phosphinites are ligands, giving derivatives similar to metal phosphine complexes. They are stronger pi-acceptors than typical phosphine ligands.

Preparation

Reactions

References

See also